OOTD Cap - Peaky Black Darlaston Shirt - CK gray/white spread collar Suit - Bonobos Gray Sharkskin PS - SoHo Black/Gray/White pattern Belt - Anson Black Leather Shoes - Brooks Brothers Black suede pennies Socks - gray WOTD - Bulova Black Classic

To celebrate my 50th (tomorrow), I've booked a trip to Chicago for the first weekend of October. I plan on attempting to reconnect with family that I haven't seen in years, and I want to visit some places I remember enjoying when I was much younger. I live in the Austin, TX area, and the shopping here is dismal. Most of the major stores are nothing more than outlets, and boutiques are rare. I'm looking for suggestions on good shopping for men's fashion. I'm not going all out for North Shore bespoke, mind you, but I do want options with quality. Clothes, hats, shoes, accessories...I'm open to all suggestions. What are some places you enjoy? As a bonus, any restaurants, food vendors, coffee houses, etc. you'd recommend? It's been a minute since I've had real Chicago pizza. Thanks! I'm sure the weather will be significantly different from Texas. Having lived in Illinois and Alaska as well, I'd like to think I'm not a huge wimp when it comes to cold! Still, I plan on taking some light clothes to keep me warm in the evenings (and there's an architecture cruise I plan to take which I'm sure will require an extra layer).

First pair of double strap monk style shoes. ID that jackets and shoe variety are my weak points right now

Tell me Gentlemen, is there a brand of denim you guys prefer over others. After watching several of the videos put out on YouTube, it's clear I need to update my wardrobe and Levi's aren't cutting it...🤣

Heading out on a date tonight. Testing the new double Monk strap shoes I got yesterday Shirt by Coofandy jeans by Izod Shoes by Santino Luciano